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glennnnn

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Do: Make it a provider that you have already met and have a good connection with.

Don't: Try someone new.

Do: Find a mutually enjoyable activity(ies) that you can do with your provider. Something as simple as a movie or dinner or perhaps a play, comedy show, art exhibit, etc.

Don't:  Allow yourself to be pressured into doing things you're not comfortable with just because it's a longer session. Sometimes providers can get a bit too comfortable with drugs, alcohol, sexual, etc. Set firm boundaries about that and if the provider does not respect your wishes, I think it's perfectly okay to pay him for the time spent but to cut off the session early.

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I'll second the make sure it is someone you've met and have a good connection with.  For an overnight, I have done everything from take a provider to a Broadway show to just staying in the room and sitting on the couch watching Jeopardy! between fuck sessions. Ironically, both of those were with the same guy on different overnights. Point is, the connection and at least some prior history is very key to making an overnight work well. 

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5 minutes ago, glennnnn said:

Thanks, guys. I hear you. I dream of waking him by sucking his cock in the morning.is this too pushy? Too invasive? Do I ask for permission each time we start a new round, a ñew activity or is permission automatically granted by the agreed overnight?

Consent is important. I would ask him about the morning thing in particular. Personally I usually have to piss really bad when I wake up so that would not be appealing to me. 

But definitely you should be able to have a few rounds of sex. To me it's not necessarily asking each time so much as we just start getting into my kissing and getting more physical. But of course if there is something you want to do specifically, just ask. 

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7 hours ago, keroscenefire said:

I would ask him about the morning thing in particular. Personally I usually have to piss really bad when I wake up so that would not be appealing to me.

I love morning sex but, besides the “piss factor” mentioned by @keroscenefire, there is also the terrible morning breath issue. Before engaging in intimate wake-up activities, which for me necessarily involve deep kissing, a quick trip to the bathroom to pee and brush my teeth (and his) is required.  And yes, there are escorts who are definitely NOT into morning sex, so the best is to ask. Once again, communication, communication, communication. 

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